“There is no distinctly native American criminal class except Congress,” Mark Twain used to joke. He was speaking from personal experience. Before his pen name became famous, Samuel L. Clemens worked in Congress, serving as an aide to Nevada Sen. William Stewart in the late 1860s, a corrupt era Twain later dubbed “the Gilded Age.” Observing Congress with a skeptical eye, Twain jotted jaded observations in a notebook: “Whiskey taken into Com.[mittee] rooms in demijohns & carried out in demagogues.”

One day, as he walked past the White House, Twain ran into his boss, who asked if he wanted to see President Ulysses S. Grant. Twain agreed, expecting to be part of a crowd of visitors. Instead, Stewart led him directly into Grant’s office, where the president sat alone at his desk, working.

“Mr. President,” the senator said, “may I have the privilege of introducing Mr. Clemens.”

“General Grant got slowly up from his table,” Twain later recalled, “put his pen down and stood before me with the iron expression of a man who had not smiled for seven years, and was not intending to smile for another seven.”

Grant shook his visitor’s hand but uttered not a word. Twain, mortified to be disturbing the president, struggled to think of something to say. “Mr. President,” he blurted out, “I—I am embarrassed. Are you?”

Grant didn’t reply. “His face broke—just a little—a wee glimmer, the momentary flicker of a summer-lightning smile, seven years ahead of time,” Twain wrote, “and I was out and gone as soon as it was.”

A decade after that inauspicious encounter, the two men met again. By then, Grant was out of office and Twain was America’s most beloved humorist. In 1879, veterans of the Union Army organized a banquet honoring Grant, their former commander, and they invited Twain to deliver a toast. Twain agreed and when he arrived in Chicago for the gala affair, the city’s mayor introduced him to Grant.

“Before I could put together the proper remark,” Twain recalled, “General Grant said, ‘Mr. Clemens, I am not embarrassed. Are you?’—and that little seven-year smile twinkled across his face again.”

At the banquet, 500 veterans feasted on oysters, roast beef, buffalo steak and breast of duck in currant jelly, each course accompanied by fine wines and champagnes. Then they loosened their belts, settled back with glasses of brandy or whiskey and listened to four hours of impassioned oratory.

There were no fewer than 15 after-dinner speakers, each instructed to deliver a toast followed by a speech. The organizers had asked Twain to toast “The Ladies,” but he declined, explaining that the ladies had been toasted so often there was nothing left to say. Instead, he suggested he toast “The Babies.” The organizers agreed and scheduled Twain to speak last, figuring that his popularity would keep people from exiting early.

As the first speaker was introduced, Twain slipped to the back of the hall to study the other orators. They were deadly serious, bellowing out florid tributes to the great general, his courageous soldiers and their glorious cause. The 14th speaker, General Thomas C. Fletcher, delivered the toast Twain had rejected—“The Ladies”—and smothered the fair sex in insipid praise: “The fires were kept by them bright upon the Altar of Home.”

Throughout this endless bombardment of orotund oratory, Grant sat still as a stone, his face as deadpan as it was the day Twain met him. “He never moved a muscle in his body for a single instant,” Twain recalled. “You could have played him on a stranger for an effigy.”

By the time General William Tecumseh Sherman introduced Twain, it was after two in the morning. As the weary crowd applauded, the humorist shuffled to the platform. He was nervous, worried that the joke that ended his speech was so outrageous that it might provoke more jeers than cheers.

“We have not all had the good fortune to be ladies,” Twain began. “We have not all been generals, or poets, or statesmen. But when the toast works down to the babies, we stand on common ground.”

That drew a laugh, which eased Twain’s nervousness somewhat. He launched into a comic riff about how a tiny baby can defeat even the bravest soldier.

“You soldiers all know that when that little fellow arrived at family headquarters you had to hand in your resignation. He took entire command. You became his lackey, his mere body servant….You could face the death-storm at Donelson and Vicksburg, and give back blow for blow. But when he clawed your whiskers and pulled your hair and twisted your nose, you had to take it.”

By now, the veterans, stuffed to their eyeballs with solemnity and eager for amusement, were roaring with laughter.

“Sufficient unto the day is one baby. As long as you are in your right mind, don’t pray for twins. Twins amount to a permanent riot. And there ain’t any real difference between triplets and an insurrection.”

Twain paused, then launched into the elaborate set-up for his final gag. Lying in their cradles today, he told the crowd, are the babies who will become the admirals, historians and presidents of tomorrow.

“And in still one more cradle, somewhere under the flag,” he said, “the future illustrious commander-in-chief of the American armies is so little burdened with his approaching grandeurs and responsibilities as to be giving his whole strategic mind at this moment to trying to find some way to get his big toe into his mouth.”

That got a laugh, and set up the joke that Twain was nervous about delivering.

“An achievement which—meaning no disrespect—the illustrious guest of this evening turned his entire attention to some 56 years ago.”

At that moment, the laughter ceased, replaced by what Twain later called “shuttering silence” in the dining hall as the veterans wondered if the speaker was insulting their general. Twain paused to let the silence deepen. Then he turned toward Grant and unleashed his final punch line.

“And if the child is but the prophesy of the man,” he said, “there are mighty few who will doubt that he succeeded.”

Grant cracked up, his stone face exploding in laughter, and his old soldiers did the same as they rose from their seats. They cheered and mobbed Twain, shaking his hand, slapping his back, praising his comic genius.

“I’ve just come to my room, Livy darling,” Twain wrote to his wife at five that morning, too excited to sleep after the long night of festivities finally ended. “For two hours and a half now, I’ve been shaking hands and listening to congratulations….Gen. Grant sat through fourteen speeches like a graven image but I fetched him! I broke him up utterly! He told me he laughed till the tears came and every bone in his body ached.”

Originally published in the February 2010 issue of American History. To subscribe, click here.

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